trans-4-(N-(2,6-dimethylphenyl)amino)stilbene | 410097-31-3

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二苯乙烯类
• 英文名称: trans-4-(N-(2,6-dimethylphenyl)amino)stilbene
• 英文别名: 2,6-dimethyl-N-[4-[(E)-2-phenylethenyl]phenyl]aniline
• CAS: 410097-31-3
• 化学式: C₂₂H₂₁N
• 分子量: 299.415
• InChiKey: YQWDYPOBLHJETF-VAWYXSNFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.5
• 重原子数：
  23
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.09
• 拓扑面积：
  12
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  trans-4-(N-(2,6-dimethylphenyl)amino)stilbene 以 正己烷 为溶剂， 生成 cis-4-(N-(2,6-dimethylphenyl)amino)stilbene
  参考文献：
  名称：

  Fluorescence Enhancement of trans-4-Aminostilbene by N-Phenyl Substitutions:  The “Amino Conjugation Effect”

  摘要：

  The synthesis, structure, and photochemical behavior of the trans isomers of 4-(N-phenylamino)stilbene (1c), 4-(A methyl-N-phenylamino)stilbene (1d), 4-(NN-diphenylamino)stilbene (le), and 4-(N-(2,6dimethylphenyl)amino)stilbene (1f) are reported and compared to that of 4-aminostilbene (1a) and 4-N,N-dimethylaminostilbene (1b). Results for the corresponding 3-styrylpyridine (2) and 2-styrylnaphthalene analogues (3) are also included. The introduction of N-phenyl substituents to 4-aminostilbenes leads to a more planar ground-state geometry about the nitrogen atom, a red shift of the absorption and fluorescence spectra, and a less distorted structure with a larger charge-transfer character for the fluorescent excited state. Consequently, the N-phenyl derivatives 1c-e have low photoisomerization quantum yields and high fluorescence quantum yields at room temperature, in contrast to the behavior of la, 1b, and most unconstrained monosubstituted trans-stilbenes. The isomerization of 1c and 1d is a singlet-state process, whereas it is a triplet-state process for le, presumably due to a relatively higher singlet-state torsional barrier. The excited-state behavior of 1f resembles 1a and 1b instead of 1c-e as a consequence of the less planar amine geometry and weaker orbital interactions between the N-phenyl and the aminostilbene groups. Such an N-phenyl substituent effect is also found for 2 and 3 and thus appears to be general for stilbenoid systems. The nature of this effect can be described as an ''amino conjugation effect''.

  DOI：

  10.1021/ja016416+
• 作为产物：
  描述：

  4-溴苄基亚磷酸二乙酯 在 tris(dibenzylideneacetone)dipalladium (0) sodium hydride 、 R-(+)-1,1'-联萘-2,2'-双二苯膦 、 sodium t-butanolate 作用下， 以 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 反应 24.33h， 生成 trans-4-(N-(2,6-dimethylphenyl)amino)stilbene
  参考文献：
  名称：

  Fluorescence Enhancement of trans-4-Aminostilbene by N-Phenyl Substitutions:  The “Amino Conjugation Effect”

  摘要：

  The synthesis, structure, and photochemical behavior of the trans isomers of 4-(N-phenylamino)stilbene (1c), 4-(A methyl-N-phenylamino)stilbene (1d), 4-(NN-diphenylamino)stilbene (le), and 4-(N-(2,6dimethylphenyl)amino)stilbene (1f) are reported and compared to that of 4-aminostilbene (1a) and 4-N,N-dimethylaminostilbene (1b). Results for the corresponding 3-styrylpyridine (2) and 2-styrylnaphthalene analogues (3) are also included. The introduction of N-phenyl substituents to 4-aminostilbenes leads to a more planar ground-state geometry about the nitrogen atom, a red shift of the absorption and fluorescence spectra, and a less distorted structure with a larger charge-transfer character for the fluorescent excited state. Consequently, the N-phenyl derivatives 1c-e have low photoisomerization quantum yields and high fluorescence quantum yields at room temperature, in contrast to the behavior of la, 1b, and most unconstrained monosubstituted trans-stilbenes. The isomerization of 1c and 1d is a singlet-state process, whereas it is a triplet-state process for le, presumably due to a relatively higher singlet-state torsional barrier. The excited-state behavior of 1f resembles 1a and 1b instead of 1c-e as a consequence of the less planar amine geometry and weaker orbital interactions between the N-phenyl and the aminostilbene groups. Such an N-phenyl substituent effect is also found for 2 and 3 and thus appears to be general for stilbenoid systems. The nature of this effect can be described as an ''amino conjugation effect''.

  DOI：

  10.1021/ja016416+

文献信息

• Fluorescence Enhancement of <i>trans</i>-4-Aminostilbene by <i>N</i>-Phenyl Substitutions:  The “Amino Conjugation Effect”
  作者：Jye-Shane Yang、Shih-Yi Chiou、Kang-Ling Liau

  DOI：10.1021/ja016416+

  日期：2002.3.1

  The synthesis, structure, and photochemical behavior of the trans isomers of 4-(N-phenylamino)stilbene (1c), 4-(A methyl-N-phenylamino)stilbene (1d), 4-(NN-diphenylamino)stilbene (le), and 4-(N-(2,6dimethylphenyl)amino)stilbene (1f) are reported and compared to that of 4-aminostilbene (1a) and 4-N,N-dimethylaminostilbene (1b). Results for the corresponding 3-styrylpyridine (2) and 2-styrylnaphthalene analogues (3) are also included. The introduction of N-phenyl substituents to 4-aminostilbenes leads to a more planar ground-state geometry about the nitrogen atom, a red shift of the absorption and fluorescence spectra, and a less distorted structure with a larger charge-transfer character for the fluorescent excited state. Consequently, the N-phenyl derivatives 1c-e have low photoisomerization quantum yields and high fluorescence quantum yields at room temperature, in contrast to the behavior of la, 1b, and most unconstrained monosubstituted trans-stilbenes. The isomerization of 1c and 1d is a singlet-state process, whereas it is a triplet-state process for le, presumably due to a relatively higher singlet-state torsional barrier. The excited-state behavior of 1f resembles 1a and 1b instead of 1c-e as a consequence of the less planar amine geometry and weaker orbital interactions between the N-phenyl and the aminostilbene groups. Such an N-phenyl substituent effect is also found for 2 and 3 and thus appears to be general for stilbenoid systems. The nature of this effect can be described as an ''amino conjugation effect''.